Author's Note:
Thank you for the overwhelmingly positive feedback!
*****
Part 4 - Monday Afternoon
You moaned in deep frustration, grinding your knees together as your empty pussy ached, denied orgasm yet again. You laid there for a few moments, your nipples pressed against the cool wood of my desk, drawing deep breaths as your cunt throbbed, trying to regain your composure as I sauntered away.
I washed and clinked around in my private bathroom. As I finished up I clapped loudly, startling you, "Freshen up, my dear. I don't know about you, but I'm famished. There's a cozy little bistro around the corner, you'll love it."
As soon as I said it, you realized that you were hungry as well. You pushed up your lithe nude form, grabbing your dress as you followed me to the washroom, slipping it on over your head with practiced ease. Which is when you noticed the pair of chrome plugs poised on a cloth on the counter along with a small bottle of lube, one plug was small and the other intimidatingly larger. The bigger one looked like it might be similar in girth to my cock...
Examining the dainty little one as you picked it up, you immediately noted how it was much heavier than it looked. Turning it over in your hands as your fingers slid over it's smooth silver curves, the faceted jewel on the end glittering.
You looked up into the mirror to see me standing behind you, the silhouette of my broad shoulders blocking the door as my strong hand came to rest on the back of your neck. "Have you ever worn a princess plug?" I asked, a lopsided grin quirking my lips.
I could see the trepidation written on your face as you gave your head a short shake, No.
"Not to worry. We will take things nice and slow." I said, winking at you as I grinned at the incongruity of my statement and the time we had spent together so far. Sliding my hand down your back as I pulled a towel off of the bar, and with a little flick of the wrist, laid it flat on on the floor. "Kneel," I commanded, continuing while you began to lower yourself, "The most important point to remember about anal penetration," I was gently pushing down on your lower back, guiding you to lay over your folded knees, "is to relax. Can you do that for me?" I lifted your dress up onto your back to display your glowing pink cheeks.
"Yes, Sir." You replied, though the tension in your back and shoulders showed me the brave face you were putting on. The little bottle of lube made a rude noise as I squirted some onto my finger behind you.
"This may be a bit cold," I warned in a silky tone. You could hear my smile in my voice.
You gasped as the cool gel on my finger touched your hot little pucker and I started stroking soft circles. You closed your eyes and began to take deep breaths, as deep as you could folded over top of your knees. Your empty pussy still aching with pent up need. Your shoulders sinking toward the floor as your hips relaxed and turned down, tilting your ass to align towards me invitingly.
Reaching over to the sink I turned on the hot water and carefully placed the small plug under the stream to warm up, my other finger stroking lazy circles around your sensitive ass. "This position you're in, with your knees to your beautiful breasts, allows everything to align internally." I spoke in calm, liquid tones as I applied just enough pressure to push the tip of my finger into your tight sphincter.
You moaned at the shallow penetration as I pulled back to stroke a few more circles before pushing back inside again. Repeating this new pattern I murmured, "Fuck you're tight, girl. We have some work ahead of us if you are ever going to take my cock in here, don't we?" I forced my slippery finger up to the first knuckle to emphasize my question.
Your breath caught in your throat before you moaned, "Yesss, Sir." Flinching as my other hand touched your horny clit again, stroking both erogenous zones together.
"Does that feel good?" I asked. Slowly, patiently pushing my finger deeper into your tight little ass with each penetration. So soon after my cock had vacated your hungry pussy this new stimulation brought you right back to the edge. I stroked my thick finger gently in and out, my other hand slipperily teasing your clit until you twitched and moaned. You were so close again.
My hands left your body. How many times had I teased you right to the edge today? I washed up in the sink and lifted the warm little plug, turning off the faucet.
You laid there breathing deeply as you heard the burp of the little bottle. My free hand came to your lower back, rubbing over the tops of your ass cheeks, still tender and glowing bright pink from your spanking, "Now be an Angel and relax for me." I purred, the tip of the plug gently but firmly pressing into your yearning ass.
"It's going in, but I assure you I will go as slowly as you need, all you have to say is 'mercy' and I will slow down." I pushed just a little harder and the crown of the plug began to stretch you with a little pinch. Your hands came out from under you at the unexpected pain.
"Mercy!" you gasped. As soon as the word left your lips the pressure receded.
"Such a good girl." I praised soothingly, pushing the plug back into your pucker more softly, massaging your tender flesh.
Slowly but insistently the solid steel plug stretched your reluctant little hole. You took a deep, controlled breath as the widest point finally popped past your stretched muscles and your hungry ass sucked it inside. All of the discomfort immediately replaced by an erotic tingle and a deep feeling of fullness, the jewelled cap nesting against your lewdly stretched cheeks.
Wringing out a warm cloth in the sink, I carefully washed all of the extra lube from your throbbing clit, before tidying up around your pretty little plug, "There we go." I said quietly, "A little constant reminder that you are my property... Stand up, please."
You felt your empty pussy twitch as you heard my words, opening your eyes as you took my offered hand and rose to your feet. Your dress poured back down to drape over your ass, hiding any sign of the toy I was subjecting you to. The weight of the plug applying a small pull to your penetrated little anus. Constricting your sphincter teased a small wave of pleasure, as did any squeezing of the muscles in your pelvic floor. You groaned as you realized that while your ass was trapped like this even doing nothing left a subtle submissive bliss radiating from your clenching little hole.
You lifted your purse to the counter, checking your make up as an anxious realization washed over you, and you paused for a moment to stare at yourself in the mirror: you were about to go out in public, again, without panties or bra, because your boss was ordering you to...
Your ass twitched and the heavy plug stroked and shifted with every quiver, sending shocks of pleasure as your cheeks flushed again. You looked back into my office, where I had unplugged my laptop, slipped it under my arm and was heading for the door.
As you followed me you began to fully realize what I had done, the heavy plug tilting left and right with each step. You gasped as the pleasurable sensations in your ass began working their magic on your teased, denied little pussy. I smiled as I handed you your light coat.
You were immediately grateful as you pulled it on, feeling very self-conscious as you covered your aroused nipples.
I held the crook of my elbow towards you, grinning as you slid your arm through mine, leaning against me as you fought with the subtle pleasure that every step was bouncing into you. Feeling that anxious tightness in your chest as we entered the elevator, every erotic footfall taking us further from the privacy of my office.
As soon as we left the building you gasped, the gentle breeze sliding up under your skirt and licking across your moist, naked lips. I loved the concentration written on your face, biting your lip as you worked to stay composed while we walked.
We rounded the corner and a new stab of worry arose as you saw a packed restaurant patio full of people enjoying their lunches. Pleasant instrumental Italian music playing over the outdoor speakers.
You blushed again when we arrived, half a dozen conversations going on around us as a small gust of wind tickled at the hem of your dress, your hand shot down over the billowy fabric even as you realized your overreaction. Flustered, you stepped aside as a few business men walked past, leaving the establishment.
A tall and slim young waiter came out to the patio and smiled at us, addressing me, "Welcome back! I think your favorite table just freed up." he said, nodding toward the interior.
"Thank you, my good man," I smiled back cordially as I slipped my hand around your waist, resting it politely but possessively on the top of your ass, guiding you inside ahead of me.
Blinking to adjust to the dimmer light within you scanned around for an empty table in the busy little place. I leaned over and spoke into your ear, "Second booth from the back." As we headed down the cozy aisle you noted that most of the diners had finished their plates, it seemed we were arriving just at the end of the lunch rush.
You walked carefully to the empty booth. The quaint red and white checkered tablecloth hanging down almost to the floor, draped over the the circular table nested within a cozy, plush three-quarter-circle bench.
I politely motioned for you to sit first, pointing to the seat that would have you facing the rear of the restaurant, "Let me take your coat, my dear."
Your stomach sank as your eyes flitted from me to our waiter while he casually looked away, "Yes, Sir... thank you, Sir." you mumbled as you slid your protection down off of your shoulders, quickly slipping into the booth.
Which was the first time your tender cheeks had touched down on something since your spanking. Your sharp hiss of breath drew a curious glance from our attentive waiter as you blushed anew and gingerly tried to find a comfortable position. While you slowly lowered yourself down the plug nestled within you began to push in deeper, applying pressure and stimulation you had never experienced before.
You took slow deep breaths as you worked at maintaining a neutral expression, shifting subtly from one cheek to the other as you tentatively settled in, stroking the plug left and right inside you. Your mind embarrassingly dancing to the thoughts of how close the straps of your dress were to slipping from your shoulders, and how only centimetres of fabric covered your bare pussy.
"Again, welcome folks," our waiter smiled, "My name is Samuel and I will be your server this afternoon." He handed us the menus, "Can I start you off with anything?"
I glanced at the little condiment stand on the table, the paper insert proclaiming Margarita Mondays! "How about a Margarita for each of us?" I asked as I slid into the booth from the other side, shuffling around until I was sitting beside you, our knees just brushing.
His eyes slid down over you, pausing for the briefest moment on your nipples, softly hinted at through the thin fabric of your dress, you nodded self-consciously as you blushed, feeling flustered yet aroused at the attention, and that I hadn't deigned to check with you before ordering, "Of course! I'll give you some time with the menus while I grab your drinks!" he smiled cheerfully, then hurried away.
